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Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346 artwork

Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346

This Week in Startups

October 5, 2026

This Week In Startups is made possible by: Today’s show: The smarter AI gets, the more it just does the work for you, and the less helpful it becomes as a tutor. Shan Reddy of Aristotle joins Jason to demo a voice-first tutor built to run a session the way a $200-an-hour human tutor would.

Speakers Jason Calacanis, Lon, Agastya, David, Ray, Shan Reddy

TopicsTechnology

SPEAKER_1 (0:00)

All right, everybody, welcome back.

Jason Calacanis (0:01)

This Week in Startups, Twist, October 2nd. Here we go, we're in the fall on, and we got a full docket and a lot of questions. People have been wanting me to do an Ask Jason, don't want to lose a minute of it. So I always like to take a moment to applaud. Sometimes, I got my new iPhone 18 Max, and then I'll just slap this on the back. There you go.

Press the button. Don't have to open my phone, just press the button, lay it on the counter. Now, I've got that incredible 360-degree microphone recording my meeting and transcribing it. What a great product. Absolutely addicting.

Lon (0:38)

If you want to go check it out for yourself, you don't have to just take our word for it. Go to plaud.ai/twist, and please use the code TWIST. It doesn't only help us out here at the program, but you are going to get 10 percent off your Plaud note pin. There you go.

Jason Calacanis (0:53)

We always applaud here. All right, let's get started. Busy day.

SPEAKER_5 (0:56)

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All right.

Lon (1:40)

Yeah, we're doing some Ask Jason. We got some live callers already in the waiting room. So I say let's admit our first caller. Welcome to the show. What's your name? Let us know your name.

Agastya (1:52)

My name is Agastya, and I'm from India.

Jason Calacanis (1:56)

Calling in from India. What time is it in India?

Agastya (2:00)

It's 10 PM right now.

Lon (2:01)

Okay.

Agastya (2:02)

All right.

Jason Calacanis (2:02)

So you got to get to bed. You got school in the morning, kid?

Agastya (2:05)

No. So I'm joining Fordham this spring.

Jason Calacanis (2:08)

Fordham University in the spring? Oh, my alma mater. Very good. Lincoln Center or Rose Hill?

Agastya (2:13)

Yeah, Rose Hill.

Jason Calacanis (2:14)

Rose Hill. Wow.

Agastya (2:16)

So I heard you went to Fordham as well.

Jason Calacanis (2:17)

I did. At the last minute in August of 1988, I got accepted as an alternate. I was going to go to Brooklyn College. I had no money. My dad's bar had been seized by the Feds because he got behind on his taxes. I had no money. But the first week of August, Edward MJ. Boland, who I had been pitching on me going to Fordham, called me up and said, Hey, Jake, thanks for all the recommendation letters and coming up and visiting me. I was pretty dogged in trying to get in. He said, I'm leaving to go to Yale to be admissions at Yale. Just wanted to let you know, before I left, I wanted to have the most promising non-traditional student get accepted to Fordham University this year. I said, who's that? He said, you. Idiot. He said, where would you like to go, Rose Hill or Lincoln Center? I said, I don't know. He goes, well, there's no housing left. I said, well, I can't afford the housing anyway, so I'm going to commute. He goes, go to Lincoln Center. I went to Lincoln Center at night and it took me four and a half years and I paid for it myself. It was $11,000 a year. I was always in arrears six to 12 months behind on my tuition, but the burst-off put me on a payment program. Somehow I squeaked through with only maybe $10,000 in Pell Grants, which are like US loans that the government gives you, and then I paid those off the year after I graduated because I got a good IT job. But yeah, you'll have a great time there. It's incredibly expensive. You must be a genius or your parents must be rich or some combination of the two. What is it, Augusta?

Parents are rich. I can tell from the roof of that marble apartment.

Your parents are doing okay.

Lon (3:45)

He's a rich genius.

Jason Calacanis (3:46)

That's incredible that you got into Fordham.

Agastya (3:48)

I think they're trying to lower acceptance rates as well, so it's pretty competitive this year from what I heard.

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